ID: ALA3908044

Max Phase: Preclinical

Molecular Formula: C19H19N5O4

Molecular Weight: 381.39

Molecule Type: Small molecule

Associated Items:

Representations

Canonical SMILES:  COCCOc1cc(NC(=O)N2CCCc3ccc(C=O)nc32)ncc1C#N

Standard InChI:  InChI=1S/C19H19N5O4/c1-27-7-8-28-16-9-17(21-11-14(16)10-20)23-19(26)24-6-2-3-13-4-5-15(12-25)22-18(13)24/h4-5,9,11-12H,2-3,6-8H2,1H3,(H,21,23,26)

Standard InChI Key:  LTZMJBMNBAPUKS-UHFFFAOYSA-N

Associated Targets(Human)

FGFR4 Tclin Fibroblast growth factor receptor 4 (3668 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Huh-7 (12904 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Fgfr4 Fibroblast growth factor receptor 4 (138 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Properties

Molecular Weight: 381.39Molecular Weight (Monoisotopic): 381.1437AlogP: 2.17#Rotatable Bonds: 6
Polar Surface Area: 117.44Molecular Species: NEUTRALHBA: 7HBD: 1
#RO5 Violations: 0HBA (Lipinski): 9HBD (Lipinski): 1#RO5 Violations (Lipinski): 0
CX Acidic pKa: 10.87CX Basic pKa: 2.36CX LogP: 2.26CX LogD: 2.26
Aromatic Rings: 2Heavy Atoms: 28QED Weighted: 0.60Np Likeness Score: -1.36

References

1.  (2016)  Ring-fused bicyclic pyridyl derivatives as FGFR4 inhibitors, 
2. Knoepfel T, Furet P, Mah R, Buschmann N, Leblanc C, Ripoche S, Graus-Porta D, Wartmann M, Galuba I, Fairhurst RA..  (2018)  2-Formylpyridyl Ureas as Highly Selective Reversible-Covalent Inhibitors of Fibroblast Growth Factor Receptor 4.,  (3): [PMID:29541363] [10.1021/acsmedchemlett.7b00485]
3. Gehringer M, Laufer SA..  (2019)  Emerging and Re-Emerging Warheads for Targeted Covalent Inhibitors: Applications in Medicinal Chemistry and Chemical Biology.,  62  (12): [PMID:30565923] [10.1021/acs.jmedchem.8b01153]
4. Fairhurst RA,Knoepfel T,Buschmann N,Leblanc C,Mah R,Todorov M,Nimsgern P,Ripoche S,Niklaus M,Warin N,Luu VH,Madoerin M,Wirth J,Graus-Porta D,Weiss A,Kiffe M,Wartmann M,Kinyamu-Akunda J,Sterker D,Stamm C,Adler F,Buhles A,Schadt H,Couttet P,Blank J,Galuba I,Trappe J,Voshol J,Ostermann N,Zou C,Berghausen J,Del Rio Espinola A,Jahnke W,Furet P.  (2020)  Discovery of Roblitinib (FGF401) as a Reversible-Covalent Inhibitor of the Kinase Activity of Fibroblast Growth Factor Receptor 4.,  63  (21.0): [PMID:32930584] [10.1021/acs.jmedchem.0c01019]